Ag(i)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4′-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides
A Ag(i)/PPh3-catalyzed chelation-controlled cycloisomerization of tryptamine-ynamide was developed to access the spiro[indole-3,4′-piperidine] scaffold in a racemic and diastereoselective manner. The diastereoselective products were achieved by a chiron approach. Density functional theory (DFT) calc...
Gespeichert in:
| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2022-03, Vol.58 (18), p.3051-3054 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3054 |
|---|---|
| container_issue | 18 |
| container_start_page | 3051 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 58 |
| creator | Chen, Yanyu Wang, Zhaobo Zhao, Wutong Sun, Shitao Lu, Yang Zhang, Junpeng Zhang, Di Cheng, Maosheng Lin, Bin Liu, Yongxiang |
| description | A Ag(i)/PPh3-catalyzed chelation-controlled cycloisomerization of tryptamine-ynamide was developed to access the spiro[indole-3,4′-piperidine] scaffold in a racemic and diastereoselective manner. The diastereoselective products were achieved by a chiron approach. Density functional theory (DFT) calculations indicated that strong non-covalent effects between the substrate and catalyst/ligand complex stabilized the spiroindoleninium intermediate via cation-π–π interactions. |
| doi_str_mv | 10.1039/d1cc07298f |
| format | Article |
| fullrecord | <record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_miscellaneous_2629055652</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2629055652</sourcerecordid><originalsourceid>FETCH-LOGICAL-j282t-ae607a4476be94cc16b95ee43eaecdf0352570d753d72e66ce6a52b5947ff8f43</originalsourceid><addsrcrecordid>eNpdjs1KAzEUhQdRsFY3PsGAmwrGZvI7syzFPyjYhYIgUtLkjk2ZTsZJWpiufAPfxUfySUzVlXdzDofvHG6SnGb4MsO0GJpMayxJkZd7SS-jgiHO8qf9necFkpTxw-TI-yWOl_G8l3yMXgf2fDidLijSKqiq24JJjVU-QAvOQwU62A2kvqvDAjz41JWpb2zrnm1tXAWIXrCv90_U2AZaa2wNL6mJbqN2PZ9urEp1pytnvVvFfBtzV__MhLZrglrFCurqqAb8cXJQqsrDyZ_2k8frq4fxLZrc39yNRxO0JDkJSIHAUjEmxRwKpnUm5gUHYBQUaFNiygmX2EhOjSQghAahOJnzgsmyzEtG-8ngd7dp3dsafJitrNdQVaoGt_YzIkiBORecRPTsH7p067aO30WKMiGozAj9BiAfeIE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2634663712</pqid></control><display><type>article</type><title>Ag(i)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4′-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Chen, Yanyu ; Wang, Zhaobo ; Zhao, Wutong ; Sun, Shitao ; Lu, Yang ; Zhang, Junpeng ; Zhang, Di ; Cheng, Maosheng ; Lin, Bin ; Liu, Yongxiang</creator><creatorcontrib>Chen, Yanyu ; Wang, Zhaobo ; Zhao, Wutong ; Sun, Shitao ; Lu, Yang ; Zhang, Junpeng ; Zhang, Di ; Cheng, Maosheng ; Lin, Bin ; Liu, Yongxiang</creatorcontrib><description>A Ag(i)/PPh3-catalyzed chelation-controlled cycloisomerization of tryptamine-ynamide was developed to access the spiro[indole-3,4′-piperidine] scaffold in a racemic and diastereoselective manner. The diastereoselective products were achieved by a chiron approach. Density functional theory (DFT) calculations indicated that strong non-covalent effects between the substrate and catalyst/ligand complex stabilized the spiroindoleninium intermediate via cation-π–π interactions.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d1cc07298f</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chelation ; Coordination compounds ; Density functional theory ; Isomerization ; Piperidine ; Stereoselectivity ; Substrates ; Tryptamines</subject><ispartof>Chemical communications (Cambridge, England), 2022-03, Vol.58 (18), p.3051-3054</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27907,27908</link.rule.ids></links><search><creatorcontrib>Chen, Yanyu</creatorcontrib><creatorcontrib>Wang, Zhaobo</creatorcontrib><creatorcontrib>Zhao, Wutong</creatorcontrib><creatorcontrib>Sun, Shitao</creatorcontrib><creatorcontrib>Lu, Yang</creatorcontrib><creatorcontrib>Zhang, Junpeng</creatorcontrib><creatorcontrib>Zhang, Di</creatorcontrib><creatorcontrib>Cheng, Maosheng</creatorcontrib><creatorcontrib>Lin, Bin</creatorcontrib><creatorcontrib>Liu, Yongxiang</creatorcontrib><title>Ag(i)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4′-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides</title><title>Chemical communications (Cambridge, England)</title><description>A Ag(i)/PPh3-catalyzed chelation-controlled cycloisomerization of tryptamine-ynamide was developed to access the spiro[indole-3,4′-piperidine] scaffold in a racemic and diastereoselective manner. The diastereoselective products were achieved by a chiron approach. Density functional theory (DFT) calculations indicated that strong non-covalent effects between the substrate and catalyst/ligand complex stabilized the spiroindoleninium intermediate via cation-π–π interactions.</description><subject>Chelation</subject><subject>Coordination compounds</subject><subject>Density functional theory</subject><subject>Isomerization</subject><subject>Piperidine</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><subject>Tryptamines</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdjs1KAzEUhQdRsFY3PsGAmwrGZvI7syzFPyjYhYIgUtLkjk2ZTsZJWpiufAPfxUfySUzVlXdzDofvHG6SnGb4MsO0GJpMayxJkZd7SS-jgiHO8qf9necFkpTxw-TI-yWOl_G8l3yMXgf2fDidLijSKqiq24JJjVU-QAvOQwU62A2kvqvDAjz41JWpb2zrnm1tXAWIXrCv90_U2AZaa2wNL6mJbqN2PZ9urEp1pytnvVvFfBtzV__MhLZrglrFCurqqAb8cXJQqsrDyZ_2k8frq4fxLZrc39yNRxO0JDkJSIHAUjEmxRwKpnUm5gUHYBQUaFNiygmX2EhOjSQghAahOJnzgsmyzEtG-8ngd7dp3dsafJitrNdQVaoGt_YzIkiBORecRPTsH7p067aO30WKMiGozAj9BiAfeIE</recordid><startdate>20220301</startdate><enddate>20220301</enddate><creator>Chen, Yanyu</creator><creator>Wang, Zhaobo</creator><creator>Zhao, Wutong</creator><creator>Sun, Shitao</creator><creator>Lu, Yang</creator><creator>Zhang, Junpeng</creator><creator>Zhang, Di</creator><creator>Cheng, Maosheng</creator><creator>Lin, Bin</creator><creator>Liu, Yongxiang</creator><general>Royal Society of Chemistry</general><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>20220301</creationdate><title>Ag(i)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4′-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides</title><author>Chen, Yanyu ; Wang, Zhaobo ; Zhao, Wutong ; Sun, Shitao ; Lu, Yang ; Zhang, Junpeng ; Zhang, Di ; Cheng, Maosheng ; Lin, Bin ; Liu, Yongxiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j282t-ae607a4476be94cc16b95ee43eaecdf0352570d753d72e66ce6a52b5947ff8f43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Chelation</topic><topic>Coordination compounds</topic><topic>Density functional theory</topic><topic>Isomerization</topic><topic>Piperidine</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><topic>Tryptamines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Yanyu</creatorcontrib><creatorcontrib>Wang, Zhaobo</creatorcontrib><creatorcontrib>Zhao, Wutong</creatorcontrib><creatorcontrib>Sun, Shitao</creatorcontrib><creatorcontrib>Lu, Yang</creatorcontrib><creatorcontrib>Zhang, Junpeng</creatorcontrib><creatorcontrib>Zhang, Di</creatorcontrib><creatorcontrib>Cheng, Maosheng</creatorcontrib><creatorcontrib>Lin, Bin</creatorcontrib><creatorcontrib>Liu, Yongxiang</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Yanyu</au><au>Wang, Zhaobo</au><au>Zhao, Wutong</au><au>Sun, Shitao</au><au>Lu, Yang</au><au>Zhang, Junpeng</au><au>Zhang, Di</au><au>Cheng, Maosheng</au><au>Lin, Bin</au><au>Liu, Yongxiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ag(i)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4′-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2022-03-01</date><risdate>2022</risdate><volume>58</volume><issue>18</issue><spage>3051</spage><epage>3054</epage><pages>3051-3054</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A Ag(i)/PPh3-catalyzed chelation-controlled cycloisomerization of tryptamine-ynamide was developed to access the spiro[indole-3,4′-piperidine] scaffold in a racemic and diastereoselective manner. The diastereoselective products were achieved by a chiron approach. Density functional theory (DFT) calculations indicated that strong non-covalent effects between the substrate and catalyst/ligand complex stabilized the spiroindoleninium intermediate via cation-π–π interactions.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1cc07298f</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2022-03, Vol.58 (18), p.3051-3054 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2629055652 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chelation Coordination compounds Density functional theory Isomerization Piperidine Stereoselectivity Substrates Tryptamines |
| title | Ag(i)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4′-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-16T20%3A16%3A54IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Ag(i)/PPh3-catalyzed%20diastereoselective%20syntheses%20of%20spiro%5Bindole-3,4%E2%80%B2-piperidine%5D%20derivatives%20via%20cycloisomerizations%20of%20tryptamine-ynamides&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Chen,%20Yanyu&rft.date=2022-03-01&rft.volume=58&rft.issue=18&rft.spage=3051&rft.epage=3054&rft.pages=3051-3054&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d1cc07298f&rft_dat=%3Cproquest%3E2629055652%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2634663712&rft_id=info:pmid/&rfr_iscdi=true |